Triethylamine → HCID 86615474, compound

Participants

Reaction Steps

To a stirred solution of keto ester 110 (4.84 g, 20 mmol) in acetonitrile (40 mL) was successively added tosyl azide (4.13 g, 21 mmol) and Et3N (4.4 g, 40 mmol). The resulting reaction mixture was concentrated after stirring for 30 min at room temperature. The diazo derivative was purified by column chromatography (silica gel; hexanes:EtOAc, 95:5) to furnish 112 (3.75 g, 70%) as an oil; IR (neat) 2141, 1713 cm−1; [α]25D=+81.0° (c 2.02, CHCl3); 1H NMR (CDCl3) δ5.77 (ddd, 1 H, J=17.3, 10.1, 7.3 Hz), 5.70 (d, 1 H, J=7.6 Hz), 5.45 (dm, 1 H, J=17.1 Hz), 5.30 (dm, 1 H, J=10.2 Hz), 5.05 (t, 1 H, J=7.5 Hz), 4.36 (q, 2 H, J=7.1 Hz), 1.74 (s, 3 H), 1.51 (s, 3 H), 1.41 (t, 3 H, J=7.1 Hz); FAB MS m/z (relative intensity) 269 (MH+, 86). This compound was used for the next step without further purification.

Provenance & Evidence